1,2-Dibromoethane → 1-(2-Bromoethoxy)-4-iodobenzene

HRID 1700889Notes

Reaction equation

HRID 1700889 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Br:9][CH2:10][CH2:11]Br.C(=O)([O-])[O-].[K+].[K+]>>[Br:9][CH2:10][CH2:11][O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 78391,2-DibromoethaneHCID 108944-IodophenolHCID 11430Potassium Carbonate

Product 1

HCID 19058471-(2-Bromoethoxy)-4-iodobenzeneYield 84%

Procedure

A mixture of 4-iodophenol (15.0 g, 68.2 mmol) and 1,2-dibromoethane (50 ml, 580 mmol) and potassium carbonate (14.0 g, 0.1 mol) was stirred and refluxed for 22 h. After cooling to r.t., the mixture was filtered, washed with ethyl acetate and concentrated in vacuo. The residue was chromatographed on silica gel (Hexane/ethyl acetate 40:1 to 20:1) to afford the title compound (18.7 g, 84%) as a white solid.

Workup

  1. temperaturerefluxed for 22 h
  2. filtrationthe mixture was filtered
  3. washwashed with ethyl acetate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel (Hexane/ethyl acetate 40:1 to 20:1)

Sources & evidence

ORD record
ord-e13ce39eeaa34889902dcc3c10961964
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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